Hydrazine hydrate (1:1) → Methyl 2-[3-(aminomethyl)piperidin-1-yl]benzoate

HRID 602165Notes

Reaction equation

HRID 602165 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][CH2:14][CH:13]([CH2:17][N:18]2C(=O)C3=CC=CC=C3C2=O)[CH2:12]1)=[O:4].O.NN>CO.O>[NH2:18][CH2:17][CH:13]1[CH2:14][CH2:15][CH2:16][N:11]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:3]([O:2][CH3:1])=[O:4])[CH2:12]1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 58992691N-[[1-[2-(Methoxycarbonyl)phenyl]piperidin-3-yl]methyl]phthalimide

Product 1

HCID 58992630Methyl 2-[3-(aminomethyl)piperidin-1-yl]benzoateYield 78%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

N-[[1-[2-(Methoxycarbonyl)phenyl]piperidin-3-yl]methyl]phthalimide (495 mg, 1.31 mmol) was dissolved in methanol (10 mL). To this solution, hydrazine monohydrate (190 μL) was added and the mixture was refluxed for 3 hours. Subsequently, the reaction mixture was diluted with water and extracted with ethylacetate. The organic layer washed with brine and dried over anhydrous sodium sulfate. Evaporation of the solvent gave 253 mg (78%) of the desired compound as an orange oil.

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. extractionextracted with ethylacetate
  3. washThe organic layer washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-88ba0a959eaf479c843f51d4b745411c
Source dataset
uspto-grants-2011_03
Patent number
US07902367B2

Reaction notes

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